Yohimbine Hydrochloride

Synopsis, Chemistry

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Also known as: 65-19-0, Yohimbine hcl, Antagonil, Yohimbe, Aphrodine hydrochloride, Yohimbine monohydrochloride

Molecular Formula

C₂₁H₂₇ClN₂O₃

Molecular Weight

390.9 g/mol

InChI Key

PIPZGJSEDRMUAW-VJDCAHTMSA-N

FDA UNII

NB2E1YP49F

A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.

1 2D Structure

Yohimbine Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

2.1.2 InChI

InChI=1S/C21H26N2O3.ClH/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1H/t12-,15-,17-,18-,19+;/m0./s1

2.1.3 InChI Key

PIPZGJSEDRMUAW-VJDCAHTMSA-N

2.1.4 Canonical SMILES

COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl

2.1.5 Isomeric SMILES

COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl

2.2 Other Identifiers

2.2.1 UNII

NB2E1YP49F

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Aphrodine Hydrochloride

2. Aphrodyne

3. Corynanthine

4. Corynanthine Tartrate

5. Hydrochloride, Aphrodine

6. Hydrochloride, Yohimbine

7. Pluriviron

8. Rauhimbine

9. Rauwolscine

10. Tartrate, Corynanthine

11. Yocon

12. Yohimbin Spiegel

13. Yohimbine

14. Yohimbine Houd

15. Yohimex

2.3.2 Depositor-Supplied Synonyms

1. 65-19-0

2. Yohimbine Hcl

3. Antagonil

4. Yohimbe

5. Aphrodine Hydrochloride

6. Yohimbine Monohydrochloride

7. Yohimbine (hydrochloride)

8. Nb2e1yp49f

9. Actibine

10. Mfcd00012674

11. 17-hydroxyyohimban-16-carboxylic Acid Methyl Ester Hydrochloride

12. Yohimbine Chloride

13. Nsc-19509

14. Yohimbin Hcl

15. Chembl537669

16. Methyl (1s,15r,18s,19r,20s)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

17. Methyl (1s,15r,18s,19r,20s)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate Hydrochloride

18. Smr000058527

19. Yohimbin Hydrochloride [usp]

20. Yohimbin Hydrochloride

21. Sr-01000597896

22. Einecs 200-600-4

23. Nsc 19509

24. Unii-nb2e1yp49f

25. Parkimbine

26. Aphrodyne

27. Gynimbine

28. Menolysin

29. Thybine

30. Tosanpin

31. Yobinol

32. Yohydrol

33. Yocon

34. Ai3-60247

35. Dayto-himbin

36. Sr-01000075297

37. Yohimbine, Hcl

38. Yohimbine Hydrochloride [usp:ban]

39. Prestwick_961

40. Nsc19509

41. Yohimbine-hydrochloride

42. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, Monohydrochloride, (16alpha,17alpha)-

43. Mls001306411

44. Mls001333983

45. Yohimbine Hydrochloride (usp)

46. Dtxsid40891272

47. Hms1569f10

48. Yohimbine Hydrochloride (antagonil)

49. (1r,2s,4ar,13bs,14as)-methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate Hydrochloride

50. Bcp19708

51. Hy-n0127

52. Nih 9689

53. Tox21_501210

54. Yohimbine Hydrochloride [mi]

55. S2373

56. Akos015951349

57. Ccg-208327

58. Cs-5238

59. Lp01210

60. Yohimbine Hydrochloride [mart.]

61. Yohimbine Hydrochloride [vandf]

62. 17alpha-hydroxy-20-alpha-yohimban-16-beta-carboxylic Acid, Methyl Ester, Hydrochloride

63. Yohimban-16-alpha-carboxylic Acid, 17-alpha-hydroxy-, Methyl Ester, Hydrochloride

64. Yohimban-16alpha-carboxylic Acid, 17alpha-hydroxy-, Methyl Ester, Monohydrochloride

65. Yohimbine Hydrochloride [usp-rs]

66. Yohimbine Hydrochloride [who-dd]

67. Ncgc00094457-01

68. Ncgc00261895-01

69. Ac-22571

70. As-13939

71. Yohimbine Hydrochloride [green Book]

72. Yohimbine Hydrochloride, Analytical Standard

73. Eu-0101210

74. N1704

75. Sw199050-2

76. Y0002

77. Yohimbine Hydrochloride [ep Monograph]

78. D06671

79. Y 3125

80. Yohimbine Hydrochloride [usp Monograph]

81. Yohimbine Hydrochloride, >=98% (tlc), Powder

82. 012y674

83. Q-201938

84. Sr-01000075297-1

85. Sr-01000597896-1

86. Sr-01000597896-4

87. Q15680050

88. 17?-hydroxyyohimban-16?-carboxylic Acid Methyl Ester Hydrochloride

89. Yohimbine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

90. Yohimbine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

91. 17.alpha.-hydroxy-20-.alpha.-yohimban-16-.beta.-carboxylic Acid, Methyl Ester, Hydrochloride

92. Yohimban-16-carboxylic Acid, 17-hydroxy-, Methyl Ester, Hydrochloride (1:1), (16alpha,17alpha)-

2.4 Create Date

2005-07-19

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₇ClN₂O₃
Molecular Weight	390.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	390.1710204 g/mol
Monoisotopic Mass	390.1710204 g/mol
Topological Polar Surface Area	65.6 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	555
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Urological Agents

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS. (See all compounds classified as Urological Agents.)

Adrenergic alpha-2 Receptor Antagonists

Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)

Mydriatics

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)